CN118027011A - Triazine compound, organic light-emitting device and display device - Google Patents
Triazine compound, organic light-emitting device and display device Download PDFInfo
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- -1 Triazine compound Chemical class 0.000 title claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000010410 layer Substances 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000004327 boric acid Substances 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 19
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 238000004949 mass spectrometry Methods 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 4
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 3
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 3
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229940126540 compound 41 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000005619 boric acid group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000004537 pulping Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- KMZUUSFWPQLMQE-UHFFFAOYSA-N 1-bromo-9,9-dimethylfluorene Chemical compound C1=CC(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 KMZUUSFWPQLMQE-UHFFFAOYSA-N 0.000 description 1
- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 1
- JESBGFNZNSEZMR-UHFFFAOYSA-N 1-bromodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C=CC=C2Br JESBGFNZNSEZMR-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical group C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 1
- SXOUNESKHJIXNK-UHFFFAOYSA-N 4-bromo-9,9-dimethylfluorene Chemical group C1=CC=C(Br)C2=C1C(C)(C)C1=CC=CC=C12 SXOUNESKHJIXNK-UHFFFAOYSA-N 0.000 description 1
- GJXAVNQWIVUQOD-UHFFFAOYSA-N 4-bromodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C(Br)=CC=C2 GJXAVNQWIVUQOD-UHFFFAOYSA-N 0.000 description 1
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical group C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
A triazine compound, an organic light-emitting device and a display device belong to the field of OLED materials. The compound has a structure shown in a formula I, a formula II, a formula III or a formula IV, has good thermal stability, film forming stability and excellent light emission performance, can be used for preparing OLED light-emitting devices, particularly used as a main material of a light-emitting layer N-type in the OLED devices, and can effectively improve the light-emitting efficiency and service life of the organic light-emitting devices.
Description
Technical Field
The present invention relates to a triazine compound that can be used for an organic light-emitting element, an organic light-emitting device using the same, and a display device, and more particularly, to a triazine compound that can be used for a light-emitting layer in an organic light-emitting element and thus realizes element characteristics such as high light-emitting efficiency, long lifetime, and low-voltage driving, an organic light-emitting device using the same, and an organic light-emitting element including the same.
Background
An Organic LIGHT EMITTING Diode (OLED) is a display device utilizing a self-luminescence phenomenon, has a large viewing angle, is thinner and thinner than a liquid crystal display device, has a faster response speed, and can realize flexible display, and thus is expected to be applied as a full-color display device or an illumination device.
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer interposed between the anode and the cathode.
Among them, the organic layer is formed of a multilayer structure of different materials in many cases, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like, in order to improve efficiency and stability of the organic light emitting element. If a voltage is applied between two electrodes in the structure of such an organic light emitting element, holes in the anode will be injected into the organic layer, and electrons in the cathode will also be injected into the organic layer, forming excitons (exciton) when the injected holes and electrons meet at the light emitting layer, which will emit photons when the excitons release energy to transition to the ground state, thereby generating light. Such an organic light-emitting element is widely known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, high-speed responsiveness, and the like.
At present, research on organic electroluminescent materials has been widely conducted in academia and industry, wherein luminescent materials are important components of organic electroluminescent devices, and there is still a great room for improvement in terms of stability and luminescence properties of the luminescent materials, which restricts industrialization of the luminescent devices. Therefore, the design and search of a compound as a novel material of the OLED to overcome the defects of the novel material in the practical application process are important points in the research work of the OLED material and the research trend in the future.
Disclosure of Invention
The invention aims to provide a triazine compound, an organic light-emitting device and a display device using the triazine compound, wherein the triazine compound has good thermal stability, and the light-emitting device prepared by the triazine compound has higher light-emitting efficiency and service life.
The invention provides a triazine compound, the structural general formula of which is shown as formula I, formula II, formula III or formula IV,
Wherein X 1 and Y 1 are different and X 1 and Y 1 are each independently selected from O, S or
Ar 1 is selected from substituted or unsubstituted C 6～C30 aromatic hydrocarbon group or C 3～C30 aromatic heterocyclic group, wherein Ar 1 is partially deuterated or completely deuterated when the compound has a structure of formula I or formula II, and Ar 1 is deuterated or non-deuterated when the compound has a structure of formula III or formula IV;
preferably, if the structure of the compound is formula I, formula II, ar 1 is selected from deuterated, or all deuterated, of the following structure:
preferably, if the structures are of formula III, formula IV, ar 1 is selected from the following structures, and deuterated or non-deuterated:
Each R 1、R2、R3、R4 is independently selected from a substituted hydrogen atom, a substituted or unsubstituted C 1～C12 alkyl group, or a substituted or unsubstituted C 6～C30 aromatic hydrocarbon group, or a C 3～C30 aromatic heterocyclic group;
And the hydrogen atoms in the compounds of formula I and formula II can be independently substituted by one of deuterium atoms, F, CN, C 1～C12 alkyl, C 1～C12 alkoxy or C 6～C30 aryl or C 3～C30 aromatic heterocyclic groups.
Preferably, the C 6～C30 aromatic hydrocarbon group is selected from phenyl, biphenyl, terphenyl, naphthyl, indenyl, fluorenyl, perylenyl, phenanthryl, pyrenyl, fluoranthenyl, or benzophenanthryl.
Preferably, the heteroatom in the C 3～C30 aromatic heterocyclyl is selected from oxygen, sulfur or nitrogen.
Preferably, the C 3～C30 aromatic heterocyclic group is selected from one of triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranodibenzothienyl, benzofuranodibenzofuranyl, benzofurocarzolyl, benzofuranothiothienyl.
Preferably, the C 3～C30 aromatic heterocyclic group is preferably one of triazinyl, dibenzofuranyl or dibenzothienyl or carbazolyl.
Preferably, the triazine compound is represented by any one of formulas 1 to 178:
the invention discloses a plurality of specific structural forms of the triazine compound, but the triazine compound is not limited to the chemical structures, and all structures of Ar 1、X1、Y1 meeting the limiting conditions are included on the basis of the structures shown in the formulas I, II, III and IV.
In a second aspect, the present invention provides an intermediate for preparing a compound of the present invention, having the structure:
In a third aspect, the present invention provides an organic electroluminescent device comprising a triazine compound as described in the first aspect.
Preferably, the organic electroluminescent device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode;
The material of the organic layer comprises the triazine compound according to the first aspect.
Preferably, the organic layer includes a light emitting layer;
the host material of the light-emitting layer comprises a triazine compound according to the first aspect.
In a fourth aspect, the present invention provides a display device comprising an organic electroluminescent device as described in the second aspect.
Compared with the prior art, the invention has the following beneficial effects:
The triazine compound obtained by designing the structure of the triazine compound has good luminous performance, can be used for preparing an organic electroluminescent device, particularly used as a luminous layer material in the organic electroluminescent device, can effectively reduce the driving voltage of the organic electroluminescent device and improves the current efficiency of the organic electroluminescent device.
Detailed Description
For a further understanding of the present invention, preferred embodiments of the invention are described below in conjunction with the examples, but it should be understood that these descriptions are merely intended to illustrate further features and advantages of the invention, and are not limiting of the claims of the invention.
Preparation example 1: synthesis of intermediate 1 and intermediate 1B
Adding 0.1mol of cyanuric chloride, 0.1mol of boric acid 1, 0.2mol of potassium carbonate, 0.005mol of tetra (triphenylphosphine) palladium and 200ml of LDMF into a reaction bottle, heating to 110 ℃ under the protection of nitrogen for reaction for 8 hours, stopping the reaction, cooling to room temperature, adding 400ml of water to separate out solid, carrying out suction filtration, pulping the obtained filter cake with ethanol at 50 ℃ for 2 hours, and carrying out suction filtration to obtain an intermediate 1-1.
0.1Mol of intermediate 1-1, 0.1mol of boric acid 2, 0.2mol of potassium carbonate, 0.005mol of tetrakis (triphenylphosphine) palladium, 300mL of toluene, 150mL of water and 0.4g of tetrabutylammonium bromide are added into a reaction bottle, the reaction is stopped under the protection of nitrogen, the temperature is raised and the reflux reaction is stopped, the reaction is cooled, the direct suction filtration is performed, the obtained filter cake is concentrated, the toluene is dissolved, the column is passed, the obtained filtrate is concentrated, and the toluene and ethanol (volume ratio 1:1) are pulped for 2 hours at 60 ℃ and the suction filtration is performed, so as to obtain the intermediate 1.
Mass spectrometry was performed on intermediate 1, and the mass spectrometry results were as follows: mass spectrum m/z:615.12. measured element content (%): c,76.01; h,3.58; cl,5.77; n,6.82.
Taking 0.01mol of intermediate 1,0.015mol of pinacol biborate, 0.03mol of potassium acetate, 0.0001mol of bis (triphenylphosphine) palladium dichloride, 50ml of toluene, heating to 110 ℃ for reflux reaction for 8 hours, adding 50ml of water, separating liquid when the mixture is hot, cooling an organic phase to 25 ℃, and directly carrying out suction filtration to obtain the intermediate 1B.
Mass spectrometry was performed on intermediate 1B to determine mass spectrum m/z:707.24. measured element content (%): c,76.39; h,4.84; n,5.94.
Referring to preparation example 1, the following intermediates can be obtained by substituting boric acid a in the following table for boric acid 1 in preparation example 1 and boric acid B for boric acid 2 in preparation example 1, with the other conditions unchanged, specifically see table 1.
TABLE 1
Preparation example 7
Adding 0.1mol of 4-bromodibenzofuran, 0.1mol of deuterated terephthaloyl acid, 0.2mol of potassium carbonate, 0.005mol of tetra (triphenylphosphine) palladium, 200mL of toluene, 100mL of water and 0.4g of tetrabutylammonium bromide into a reaction bottle, heating and refluxing under the protection of nitrogen for 6 hours, stopping the reaction, cooling, directly performing suction filtration, adding the obtained filter cake into a mixed solution of 20g of hydrochloric acid and 200mL of ethanol and 20mL of water, refluxing and stirring for 2 hours, directly performing suction filtration, concentrating the obtained filtrate to dryness, and pulping with n-heptane to obtain boric acid 7.
To verify the structure of boric acid 7, boric acid 7 pinacol ester is prepared by reflux reaction of 0.5 g of boric acid 7, 2g of pinacol and 20 ml of toluene for 6 hours, and the gas phase mass is measured after the reaction solution is diluted, wherein the mass spectrum m/z of a main peak is as follows: 374.2. preparation example 8 where the obtained boric acid 7 is the target product
Referring to preparation 7, 4-bromodibenzothiophene was used instead of 4-bromodibenzofuran, and other operations did not give boric acid 8
Preparation example 9
Referring to preparation 7, 1-bromo-9, 9-dimethylfluorene was used instead of 4-bromodibenzofuran, and boric acid 9 preparation 10 could be obtained without any change in other operations
Referring to preparation 7, boric acid 10 can be obtained by using 1-bromodibenzofuran instead of 4-bromodibenzofuran and other operations
PREPARATION EXAMPLE 11
Referring to preparation 7, 1-bromodibenzothiophene was used instead of 4-bromodibenzofuran, and other operations were unchanged to give boric acid 11, preparation 12
Referring to preparation 7, boric acid 12 can be obtained by substituting 4-bromo-9, 9-dimethylfluorene for 4-bromodibenzofuran and other operations
Referring to preparation example 1, the following intermediates can be obtained by substituting boric acid a in the following table for boric acid 1 in preparation example 1 and boric acid B for boric acid 2 in preparation example 1, with the other conditions unchanged, specifically see table 2.
TABLE 2
Synthesis example 1: synthesis of Compound 1
To a reaction flask were added 0.01mol of intermediate 1, 0.01mol of deuterated phenylboronic acid, 0.02mol of potassium carbonate, 0.0005mol of tetrakis (triphenylphosphine) palladium, 60mL of toluene, 30mL of ethanol and 30mL of water, and the mixture was heated under reflux under nitrogen protection for 6 hours, the reaction was stopped, the mixture was cooled and filtered directly, the obtained cake was concentrated with toluene and then passed through a column, and the obtained filtrate was concentrated and recrystallized with toluene to obtain compound 1.
Mass spectrometry was performed on compound 1, and the mass spectrometry results were as follows: mass spectrum m/z:662.22.
Synthesis example 2: synthesis of Compound 41
To a reaction flask were added 0.01mol of intermediate 2B, 0.01mol of bromo-1, 0.02mol of potassium carbonate, 0.0005mol of tetrakis (triphenylphosphine) palladium, 70mL of toluene, 35mL of ethanol and 35mL of water, and the mixture was heated under reflux under nitrogen for 6 hours, the reaction was stopped, the mixture was cooled and filtered directly by suction, the obtained cake was concentrated by toluene and then passed through a column, and the obtained filtrate was concentrated and recrystallized by toluene to obtain compound 41.
Mass spectrometry was performed on compound 41, and the following mass spectrometry results were obtained: mass spectrum m/z:829.39.
Synthesis example 3: synthesis of Compound 48
Referring to synthesis example 2, substituting intermediate 4B for intermediate 2B and substituting deuterated 1-bromonaphthalene for bromo-1, the other conditions were unchanged, to afford compound 48.
Mass spectrometry was performed on compound 48 to obtain the following mass spectrum results: mass spectrum m/z:714.25.
Synthesis example 4: synthesis of Compound 58
Referring to synthetic example 2, substituting intermediate 6B for intermediate 2B and substituting deuterated 9-bromophenanthrene for bromo 1, the other conditions were unchanged, yielding compound 58.
Mass spectrometry was performed on compound 58 and the following mass spectra were obtained: mass spectrum m/z:792.33.
Other compounds can be obtained in a similar synthetic manner.
In the invention, the specific structure of the materials used in the following device application examples is as follows:
In the invention, TCTA is taken as a P-type main body material, the compound is taken as an N-type main body material, N-1, N-2, N-3, N-4 and N-5 are taken as N-type main body materials for comparison examples, firpic is taken as a light-emitting layer doping material to prepare the organic electroluminescent device, and specific device embodiments are as follows
Device example 1
Device example an organic electroluminescent device was provided, with the compound 1 provided in synthetic example 1 of the present invention as the host material for the N-type light-emitting layer; the organic electroluminescent device structure is as follows:
ITO/HT (40 nm)/luminescent layer host material (TCTA: compound 1): firpic 5% (30 nm)/TPBI (30 nm)/LiF (0.5 nm)/Al (150 nm).
The preparation method of the organic electroluminescent device comprises the following steps:
The glass substrate coated with the ITO transparent conductive layer (serving as an anode) is subjected to ultrasonic treatment in a cleaning agent, then washed in deionized water, then subjected to ultrasonic degreasing in a mixed solvent of acetone and ethanol, then baked in a clean environment until the water is completely removed, cleaned by ultraviolet light and ozone, and bombarded on the surface by a low-energy cation beam so as to improve the property of the surface and the bonding capability with a hole layer.
Placing the glass substrate with the anode in a vacuum cavity, vacuumizing to 1X 10-5-9X 10-4Pa, and vacuum evaporating a hole transport layer HT on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40nm;
Vacuum evaporating a main material and a doping material Firpic on the hole transport layer to serve as a light-emitting layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30nm; wherein, the main material of the luminescent layer (TCTA: compound 1): firpic 5% (30 nm) refers to the ratio of TCTA in the device: compound 1: firpic is co-evaporated to form a light emitting layer at a mass ratio of 57:38:5, the thickness of the light emitting layer being 30nm.
Sequentially vacuum evaporating an electron transport layer TPBI on the light-emitting layer, wherein the evaporation rates are 0.1nm/s, and the evaporation film thicknesses are 30nm respectively;
LiF of 0.5nm and Al of 150nm are vacuum evaporated on the electron transport layer as an electron injection layer and a cathode.
Device examples 2 to 20
Device examples 2 to 20 each provided an organic electroluminescent device differing from device example 1 only in the light-emitting layer N-type host material (see table 3 below), and the other conditions were the same as device example 1.
Device comparative examples 1 to 5
Device comparative examples 1 to 5 each provided an organic electroluminescent device differing from device example 1 only in the light-emitting layer N-type host material (see table 3 below), and the other conditions were the same as device example 1.
Performance testing
The testing method comprises the following steps: testing the driving voltage, the current efficiency and the service life LT95 of the OLED device by using an OLED-1000 multichannel accelerated aging service life and photochromic performance analysis system manufactured by Hangzhou remote production; the LT95 refers to the time required for maintaining the current density at the initial luminance of 1000nit and reducing the luminance to 95% of the original luminance, and the test items include luminance, driving voltage and current efficiency of the organic electroluminescent device, and the driving voltage and current efficiency and LT95 data are all relative values at the luminance of 1000cd/m 2. The performance test results of the organic electroluminescent device are shown in the following table 3:
TABLE 3 Table 3
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As is clear from the contents of Table 3, the present invention provides triazine compounds by molecular design. The triazine compound provided by the invention can be used as an N-type main material of a luminous layer of an OLED luminous device, so that the OLED luminous device has lower driving voltage, higher current efficiency and longer service life.
The detailed process flow of the present invention is described by the above embodiments, but the present invention is not limited to the above detailed process flow, i.e., it does not mean that the present invention must be implemented depending on the above detailed process flow. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (10)
1. The triazine compound is characterized by having a structural general formula shown in formula I, formula II, formula III or formula IV:
Wherein X 1 and Y 1 are different and X 1 and Y 1 are each independently selected from O, S or
Ar 1 is selected from substituted or unsubstituted C 6～C30 aromatic hydrocarbon group or C 3～C30 aromatic heterocyclic group, wherein Ar 1 is partially deuterated or completely deuterated when the compound has a structure of formula I or formula II, and Ar 1 is deuterated or non-deuterated when the compound has a structure of formula III or formula IV;
preferably, if the structure of the compound is formula I, formula II, ar 1 is selected from deuterated, or all deuterated, of the following structure:
Preferably, if the structure of the compound is formula III, formula IV, ar 1 is selected from the following structures, and deuterated or non-deuterated:
Each R 1、R2、R3、R4 is independently selected from a substituted hydrogen atom, a substituted or unsubstituted C 1～C12 alkyl group, or a substituted or unsubstituted C 6～C30 aromatic hydrocarbon group, or a C 3～C30 aromatic heterocyclic group;
and the hydrogen atoms in the compounds of formula I, formula II, formula III, formula IV may each independently be substituted with one of deuterium atoms, F, CN, C 1～C12 alkyl, C 1～C12 alkoxy or C 6～C30 aryl or C 3～C30 aromatic heterocyclic groups.
2. The triazine compound according to claim 1, wherein the C 6～C30 aromatic hydrocarbon group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, indenyl, fluorenyl, perylenyl, phenanthryl, pyrenyl, fluoranthenyl, and benzophenanthryl.
3. A triazine compound according to claim 1, wherein the heteroatom in the C 3～C30 aromatic heterocyclic group is oxygen, sulfur or nitrogen.
4. A triazine compound according to claim 3, wherein the C 3～C30 aromatic heterocyclic group is selected from any one of triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzofuranodibenzothienyl, benzofuranodibenzofuranyl, benzofurocarzolyl, benzofuranothiothienyl;
Preferably, the C 3～C30 aromatic heterocyclic group is selected from any one of triazinyl, dibenzofuranyl, dibenzothienyl or carbazolyl.
5. The triazine compound according to any one of claims 1 to 4, wherein the triazine compound has a structure as shown in any one of formulae 1 to 178:
and the hydrogen atoms in formulas 1 to 178 may be substituted in whole or in part with deuterium atoms.
6. An intermediate having the structure:
The intermediate is used for preparing the triazine compound as claimed in any one of claims 1 to 5.
7. An organic light-emitting device comprising the triazine compound according to any one of claims 1 to 5.
8. The organic light-emitting device according to claim 7, wherein the organic light-emitting device comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer comprises the triazine compound according to any one of claims 1 to 5.
9. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer, and a host material of the light-emitting layer comprises the triazine compound.
10. A display device comprising the organic light-emitting device according to any one of claims 7 to 9.
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